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Bernina Pass from Tirano

My wife and I with another couple will be in Tuscany for a week then headed to northeast Italy after wards to visit relatives and hang out a few days. My wife wants to go to Prague from there spend three to four days then head home (US) from there. I have been advised that air is the only viable means to get there considering the distance, train is a long excursion.
I am thinking we could head over to Switzerland via the Bernina Pass train and then tour the sites there. Headed to Tirano from Venice might be an equally daunting excursion. I'd like any suggestions out there and maybe even another option? I'd love the Alps and am looking to head that way. Maybe Prague is the best choice?

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The Bernina Express scenic train departs twice daily from Tirano at 08:50 and 14.33. The journey to St. Moritz takes about 2.5hrs. However, the train journey from Venice to Tirano takes close to 6.0 hours with one train change at Milan. To make the 14:33 run, you would need to depart Venice at 6:58. It's the only run that can get you there in time on the same day. Your journey from Venice to Prague by train will take close to 14.0hrs with at least 2-3 changes. You might look into a budget airline flight from Marco Polo to Prague.